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Despite widespread changes to teacher evaluation in the past 5 years, scant research has examined the experiences of perhaps the most important participant in a teacher’s evaluation: the principal. Using in-depth interviews with 20 school leaders in year 2 of a new evaluation system, and follow-up interviews with the same leaders in year 4, this paper examines New Haven (CT) Public Schools’ efforts to reform teacher evaluation from the perspective of school leaders. I find that leaders began the initiative cautiously optimistic about its potential, but expressed less faith in the system after four years of using it. This decline in optimism among leaders was related to their experiences with attempting to dismiss under-performing teachers based on evaluations.